The regioselective synthesis of the methyl-ionone isomers 6-9 is described. The enantiomers of the 7-isomers 8 and 9 are prepared by enzyme-mediated resolution of the corresponding 4-hydroxy derivatives followed by reductive elimination of the hydroxy group. The absolute configuration of the latter compound is determined by chemical correlation with the known alpha-isomers. Since all the isomers obtained are components of the artificial violet odourants sold under the trade name of Iralia (R), their odour properties are evaluated by professional perfumers.
Synthesis, olfactory evaluation and determination of the absolute configuration of the beta- and gamma-Iralia (R) isomers
Fuganti C;Serra S
2008
Abstract
The regioselective synthesis of the methyl-ionone isomers 6-9 is described. The enantiomers of the 7-isomers 8 and 9 are prepared by enzyme-mediated resolution of the corresponding 4-hydroxy derivatives followed by reductive elimination of the hydroxy group. The absolute configuration of the latter compound is determined by chemical correlation with the known alpha-isomers. Since all the isomers obtained are components of the artificial violet odourants sold under the trade name of Iralia (R), their odour properties are evaluated by professional perfumers.File in questo prodotto:
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